amyl nitrite

Small moleculeexperimental

Nitrite Ion is a symmetric anion with equal N–O bond lengths. Nitrite is important in biochemistry as a source of the potent vasodilator nitric oxide. Nitrate or nitrite (ingested) under conditions that result in endogenous nitrosation has been classified as "Probably carcinogenic to humans" (Group 2A) by International Agency for Research on Cancer (IARC), the specialized cancer agency of the World Health Organization (WHO) of the United Nations. Sodium nitrite is used for the curing of meat because it prevents bacterial growth and, as it is a reducing agent (opposite of oxidation agent), in a reaction with the meat's myoglobin, gives the product a desirable pink-red "fresh" color, such as with corned beef. This use of nitrite goes back to the Middle Ages, and in the US has been formally used since 1925. Because of the relatively high toxicity of nitrite (the lethal dose in humans is about 22 milligrams per kilogram of body weight), the maximum allowed nitrite concentration in meat products is 200 ppm. At these levels, some 80 to 90% of the nitrite in the average U.S. diet is not from cured meat products, but from natural nitrite production from vegetable nitrate intake. Under certain conditions – especially during cooking – nitrites in meat can react with degradation products of amino acids, forming nitrosamines, which are known carcinogens. However, the role of nitrites (and to some extent nitrates) in preventing botulism by preventing C. botulinum endospores from germinating have prevented the complete removal of nitrites from cured meat, and indeed by definition in the U.S., meat cannot be labeled as "cured" without nitrite addition. They are considered irreplaceable in the prevention of botulinum poisoning from consumption of cured dry sausages by preventing spore germination. Nitrite is a member of the drug class antidotes and is used to treat Cyanide Poisoning. — NCATS

Clinical trial activity

6 trials · 8 clinical orgs · 0 marketing orgs

Phase 1
1
Phase 2
2
Phase 3
0
Phase 4
1

Earliest trial started Jan 1, 2010 (NCT01178359)

Timeline

2010s

  1. Jan 1, 2010

    Earliest Phase 1 Sponsor(trial)

  2. Jan 1, 2012

    Earliest Phase 2 Sponsor(trial)

Indications

Approved for

Mechanism of action

  • Unspecified targetOTHER

    Unknown

    Amyl nitrite cause direct vasorelaxation through vascular generation of nitric oxide (NO) and relaxation via a cyclic guanosine monophosphate-dependent process.

Chemistry & pharmacology

Loading structure…

SMILES

[O-]N=O
Mol. weight
46.0055 g/mol
Chirality
Achiral Molecule
Inorganic
No
Polymer
No

Oral

No

Parenteral

No

Topical

No

Sources

Also known as

  • 1-nitropentane
  • 1-nitropentane
  • amylnitrit
  • amyl nitrite
  • amyl nitrite
  • amyl nitrite
  • amyl nitrite
  • amyl nitrite
  • amyl nitrite
  • amyl nitrite
  • amyl nitrite
  • amyl nitrite
  • n-amyl nitrite
  • n-amyl nitrite
  • nitramyl
  • nitramyl
  • nitramyl
  • nitrite
  • nitrite
  • nitrite
  • nitrite anion
  • nitrite anion
  • nitrite ion
  • nitrite ion
  • n-pentyl nitrite
  • n-pentyl nitrite
  • pentyl nitrite
  • pentyl nitrite
  • vaporole

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT04905173N/ANov 30, 2021Mayo Clinic
NCT02463357Phase 4Aug 1, 2015Alma College, University of Colorado, University of Colorado, Denver
NCT02428959N/AJun 1, 2014Johns Hopkins University
NCT01932606Phase 2Aug 1, 2013Mayo Clinic
NCT01431313Phase 2Apr 1, 2012University of Pittsburgh
NCT01178359Phase 1Jan 1, 2010Medic One Foundation, University of Washington
Showing 6 of 6 trials
Page 1 / 1

Organizations

Research & Development (8)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
Mayo ClinicAcademic/Hospital2222013
Alma CollegeAcademic/Hospital1012015
Johns Hopkins UniversityAcademic/Hospital1112014
Medic One FoundationAcademic/Hospital1012010
University of ColoradoAcademic/Hospital1012015
University of Colorado, DenverAcademic/Hospital1112015
University of PittsburghAcademic/Hospital1112012
University of WashingtonAcademic/Hospital1112010
8 organizations
Page 1 / 1